Vesicles Comprising Dimethylaminopropyl Octadecanamide, Stearic Acid, and Carboxyhexadecyl Disulfide and Their Release P
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pISSN 1226-8372 eISSN 1976-3816
RESEARCH PAPER
Vesicles Comprising Dimethylaminopropyl Octadecanamide, Stearic Acid, and Carboxyhexadecyl Disulfide and Their Release Property under Reducing Condition Jin Ah Kim and Jin-Chul Kim
Received: 2 December 2019 / Revised: 28 February 2020 / Accepted: 22 March 2020 © The Korean Society for Biotechnology and Bioengineering and Springer 2020
Abstract Vesicles comprising dimethyl aminopropyl octadecanamide (DMAPODA), stearic acid (SA), and carboxyhexadecyl disulfide (CHDDS) were prepared as reduction-responsive carriers. Vesicular particles were found on TEM micrographs and the diameter fell within 100-400 nm. The hydrodynamic mean diameter increased with increasing the content of CHDDS. The zeta potential was lowered by the incorporation of CHDDS into the vesicular membrane. Vesicle whose DMAPODA/SA/ CHDDS molar ratio was 1/1/5 exhibited one endothermic peak around 50.9°C, indicating that the vesicular membrane was homogeneous in the composition. Strong signals were found in 500-540 cm-1 in the Raman spectrum of vesicles, suggesting that the disulfide lipid (i.e. CHDDS) was incorporated into the vesicular membranes. Vesicles containing CHDDS released rhodamine B in dithiothreitol (DTT, a reducing agent) concentration-dependent manner. The DTTsensitivity of the vesicles in terms of release was higher as the CHDDS content was higher. Keywords: dimethyl aminopropyl octadecanamide, carboxyhexadecyl disulfide, vesicular carrier, reductioninduced release, rhodamine B
Jin Ah Kim, Jin-Chul Kim* Department of Medical Biomaterials Engineering, College of Biomedical Science and Institute of Bioscience and Biotechnology, Kangwon National University, Chuncheon 24341, Korea Tel: +82-33-250-6561; Fax: +82-33-259-5645 E-mail: [email protected]
1. Introduction The spontaneous self-assembling phenomena of amphiphilic molecules take places in aqueous phase by entropy-driven process [1-4]. Different kinds of self-assemblies are formed, depending on the packing parameter of the amphiphilic molecules [3,5-8]. When the packing parameter is around 1, the amphiphilic molecules are rectangular and they are able to be assembled to form bilayer vesicles (Packing parameter = V/LA, where, V is the volume of hydrophobic tail, L is the length of hydrophobic tail, and A is the area of hydrophilic head). Phosphatidylcholine is a representative building block which can constitute bilayer vesicles. When the packing parameter is greater than 1, the amphiphilic molecules are triangular and they can be assembled into reversed hexagonal phase. Dioleoylphosphatidylethanolamine (DOPE) is one of building blocks for the formation of reversed hexagonal phase. DOPE can also constitute bilayer vesicles if complementary amphiphiles are intercalated among the phospholipid molecules [9-11]. Palmitoyl immunoglobulin G is a representative complementary molecule and it could stabilize the DOPE bilayer [12]. When the packing parameter is less than 1, the amphiphilic molecules are conical and they can form micelles. One
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